Location: Longboat Key
Keyword(s): Martha B. King Middle
Keyword(s) Middle School: Martha B. King Middle
Do Not Show Listings
6489 GULFSIDE RD, LONGBOAT KEY, FL 34228
$13,995,000161 Days on yellowkey MLS ID: A4677413
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 6616 Built: 2026 Tax: $42,641 (2025)Community: Sleepy LagoonSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$42,641
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: This Seaward Homes Curated Collection residence at 6489 Gulfside is ready for occupancy. Enjoy the ultimate Longboat Key lifestyle with your own direct Gulf-front private access and stunning views of the Gulf of Mexico. Designed by DSDG Architects, this home epitomizes exceptional quality and attention to detail. Come and witness the cutting edge of enhanced hurricane construction, wander and enjoy the exquisite staging by Clive Daneil Homes. Situated on a coveted 90' Gulf/Beach-front lot, the property offers soft sands, endless Gulf views, and miles of walkability. In 2025, Longboat Key completed a significant beach re-nourishment project, giving Gulfside Road homeowners one of the widest and deepest stretches of beach on the entire island. Equally notable, Gulfside Road is one of the rare Gulf-side streets set back from the main highway, offering a tranquil, private environment that feels worlds away from the activity of Gulf of Mexico Drive. The main house, elevated over 15 feet, features 11' ceilings, four oversized en-suite bedrooms, and more than 6,600 sq ft of air-conditioned living space, including a grade-level, air-conditioned multipurpose room that can be tailored for wellness, fitness, or a variety of additional lifestyle needs. The wide-open floor plan, generous room sizes, and large impact-rated safety glass sliding doors and windows fill the home with natural light. Two nearly 40' terraces on the main and second floors provide ideal spaces to enjoy the outdoor island lifestyle and breathtaking Gulf views. Interior finishes by Studio G Homes elevate luxury living to the next level. The interior finishes include large-format porcelain tile and hardwood flooring, Italian-imported cabinetry, a custom floating steel-and-wood staircase, a three-stop elevator, 8' solid interior doors, high-efficiency mechanical systems, a top-of-the-line Thermador™ appliance package, AXOR™ and Hansgrohe™ plumbing fixtures, temperature-controlled wine storage, and detailed AV, lighting control, and security systems. Exterior features include solid concrete and masonry construction on all floors, a deep concrete piling foundation for added strength, Longboard™ premium aluminum architectural details, and a fine light-sand exterior stucco finish. The resort-like pool area and custom spa are surrounded by a lush tropical landscape package. The garage accommodates four cars, with the option to add car lifts. Longboat Key, an 11-mile barrier island, is just minutes from St. Armands Circle and downtown Sarasota. The Sarasota Bradenton International Airport is approximately 25 minutes away. Embrace the opportunity to own this unparalleled residence and experience the pinnacle of coastal luxury living.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Nicholle Mckiernan (941-928-2922)
605 SUTTON PL #201, LONGBOAT KEY, FL 34228
$619,00091 Days on yellowkey MLS ID: A4687586
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1148 Built: 1973 Tax: $6,756 (2025)Community: Sutton PlaceCondo
Taxes:$6,756
Remarks: This is the one you have been waiting for!! INCREDIBLE UNOBSTRUCTED BAY VIEWS & BREATHTAKING SUNRISES from this light-filled CORNER unit in the beach-to-bay community of Sutton Place. Enjoy stunning vistas from nearly every room through impact windows and doors! Meticulously maintained and beautifully renovated, this spacious two-bedroom, two-bath coastal retreat is truly exceptional. The thoughtfully designed open concept chef’s kitchen with premium cabinetry, plentiful storage, and Cambria quartz countertops seamlessly connects to the expansive living area through a custom dining island with wraparound seating. Plantation shutters throughout the kitchen and living area add to the coastal island feel. The enclosed lanai, featuring walls of glass that span along the rear of the unit, provides an ideal setting for morning coffee, evening relaxation, remote work, or accommodating additional guests. The spacious primary and secondary bedrooms provide exceptional views, each with direct access to the lanai through impact-rated sliding doors. The serene primary bedroom boasts a generous walk-in closet fitted with a custom organizer and an elegantly renovated bathroom with a walk-in shower, complete with a linen closet. The secondary bedroom offers ample storage with a double closet, also fitted with custom organizers. The adjacent guest bath has been tastefully renovated. Parking is easy with a covered, assigned space in a convenient location, plus plenty of overflow and guest parking. While the stairs are easily accessible; there is also an elevator for added convenience. The in-building storage unit provides extra space for any additional storage needs. Sutton Place offers a wide range of amenities, including two heated swimming pools, a community clubhouse, marina facilities with boat slips (current wait list but only $300 annually!!), kayak storage equipped with electric launch, a fish cleaning station, designated grilling areas, car wash stations, and deeded beach access with private beach pavilion featuring storage lockers, showers, and restrooms. The community successfully endured the recent storms, experiencing minimal overall damage and no impact to any individual units. With its exceptional location, unmatched views, and wonderful amenities, this property is an opportunity not to be missed! Schedule your private showing today!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Melissa Rodocker (703-969-2345)
4976 GULF OF MEXICO DR #Villa 18, LONGBOAT KEY, FL 34228
$600,000276 Days on yellowkey MLS ID: A4665034
REDUCED by $50,000 (7.7%) on 05/30/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1900 Built: 1974 Tax: $5,878 (2024)Community: Windward BaySpa: NoVilla
Taxes:$5,878
Tax Year: 2024
Remarks: Virtually Staged. PRICE REDUCED! Experience the ultimate Longboat Key lifestyle in this waterfront gem featuring stunning Sarasota Bay and canal views. This spacious residence offers two Bedrooms, two Bathrooms, a versatile Bonus Room (ideal as a 3rd Bedroom, Home Office or private In-Law/Nanny Suite), plus a generous laundry room with newer full-size machines. This villa has been completely and meticulously renovated, with no detail overlooked and no expense spared. Beyond its stunning finishes, this home offers something incredibly valuable: Exceptional Peace of Mind! Major infrastructure updates include new electrical and plumbing systems, new Luxury Vinyl Plank flooring, fresh interior paint, and Hurricane-Impact Windows and Doors throughout. EVEN BETTER...exterior Building Maintenance Repairs and Insurance (including Flood, Hurricane, and Hazard coverage) are all included in the monthly HOA fee, creating a truly low-stress ownership experience. Recent updates include stylishly renovated bathrooms with stone countertops and new vanities, while the spacious new kitchen offers stainless appliances, quartz counters, plus abundant storage and counter space. This home also features a light-filled Florida room opening to a private patio, perfect for outdoor grilling, dining under the stars or watching playful manatees and dolphins in the canal. And for ultimate convenience, everyday living is effortless with the attached covered carport. Beyond your private retreat, Windward Bay offers resort-style amenities across 26 pristine, landscaped bay front acres. Enjoy two heated pools with complimentary lounge seating, saunas, tennis and pickleball courts, a fitness center, shuffleboard, boat slips ($50/month or $55/month with owner-provided lift), kayak/paddle board storage and launch ($45/year), fishing, and three private beach access points. Plus, Zota Beach Resort is just across the street for elegant dining and nightly sunsets. Windward Bay is a proactive, well-managed community that has passed its structural integrity inspection and is certified for another 10 years. Owners may rent up to twice per year with a one-month minimum, offering excellent income potential. Best of all—this rare Longboat Key community is pet-friendly for Owners and Renters! Don’t miss your chance to own a slice of island paradise and enjoy a relaxed, coastal lifestyle surrounded by natural beauty and first-class amenities. Your dream retreat awaits!
Listing Agent: Christina Weger (941-773-4154)
4310 FALMOUTH DR #304, LONGBOAT KEY, FL 34228
$330,000161 Days on yellowkey MLS ID: A4678473
REDUCED by $20,000 (5.7%) on 06/18/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 747 Built: 1969Monthly Fee: $1,196 Tax: $4,937 (2025)Community: Longboat HarbourCondo
Taxes:$4,937
Remarks: Unlock the Door to Your Dream Beach and Boating Lifestyle! Step into a world of unparalleled charm with this move-in ready, fully furnished gem on Longboat Key. This isn’t just a home; it’s a transformative lifestyle choice for those craving adventure, relaxation, and vibrant social connections. Picture yourself waking up to breathtaking bay views every morning from your stylish condo, featuring elegant granite countertops, state-of-the-art appliances, and a spa-like shower that redefines luxury. Your perfect beach days await with exclusive private beach access, complete with a dedicated beach house that offers showers and restrooms for your convenience. For boating enthusiasts, the Longboat Key Yacht Club provides convenient boat slips and kayaks, giving you immediate access to the pristine waters of the bay. Stay energized and engaged with an array of top-tier amenities, including tennis courts, shuffleboard, a rejuvenating sauna, and a fully equipped gym. Join a dynamic social scene filled with workshops, a cozy library, an inspiring art studio, and clay classes, plus the warm camaraderie of the Book Buddies club that fosters connections. With four inviting swimming pools, a grand banquet hall for gatherings, a fun game room for entertainment, and convenient private beach parking, every day feels like a luxurious getaway. This is more than just a condo; it’s a lifestyle experience you truly deserve. Don’t let this extraordinary Longboat Key oasis pass you by! Schedule your showing today and discover if it’s your perfect match!
Listing is courtesy of: HOUSE MATCH (941-213-7028)
Listing Agent: Rachel Rademacher (612-965-6188)
4234 GULF OF MEXICO DR #E2, LONGBOAT KEY, FL 34228
$580,000252 Days on yellowkey MLS ID: A4667654
REDUCED by $18,000 (3.0%) on 06/04/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1150 Built: 1973 Tax: $10,617 (2025)Community: Pelican Harbour & Beach ClubCondo
Taxes:$10,617
Remarks: REDUCED AND INCREDIBLE VALUE! EXCEPTIONAL FULL BAY VIEWS, PRIVATE BEACH ACCESS AND KAYAK LAUNCH, HURRICANE-RATED WINDOWS AND SLIDERS, UPDATED BATHS AND MORE! This 2BR/2BA retreat at Pelican Harbour & Beach Club delivers the quintessential Longboat Key lifestyle. From its 2nd-floor vantage point, enjoy peaceful sunrises over the Bay and the tranquil fountain view from your screened lanai, surrounded by lush tropical landscaping. Then, end your day with spectacular Gulf sunsets and leisurely beach walks from your private beach access. The updated kitchen gleams with new 2025 solid quartz countertops, stainless Samsung appliances, a tile backsplash, and a breakfast bar island—perfect for entertaining. Open living and dining areas flow seamlessly toward the water, creating a bright, inviting space ideal for relaxing or hosting friends. The spacious owner’s suite opens to the lanai and features a 2023-renovated ensuite bath with stone countertops, dual sinks, porcelain tile flooring, a glass shower, and custom closets. The guest suite offers another beautifully updated bath and generous storage. Additional highlights in-unit laundry, 2023 roof, 2024 exterior paint, and a hurricane-rated carport conveniently located just outside your door. This unit is currently rented, and tenants will vacate or stay so you can continue to earn rental income immediately! Ideally situated mid-island, Pelican Harbour & Beach Club offers outstanding amenities: Bay and beach access, first-come dock slips, a heated resort-style pool, two newly resurfaced tennis/pickleball courts, a clubhouse with social activities, kayak storage and launch, bike storage, and ample owner storage. This pet-friendly, rental-friendly community welcomes large dogs and seasonal visitors and perfectly combines luxury, flexibility, and coastal charm—just minutes from Bayfront Park, the new St. Regis Resort, St. Armands Circle, and downtown Sarasota’s vibrant restaurants, culture, and shopping.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lenore Treiman (941-356-9642)
615 DREAM ISLAND PL #105, LONGBOAT KEY, FL 34228
$949,00073 Days on yellowkey MLS ID: A4689957
REDUCED by $46,000 (4.6%) on 06/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1293 Built: 1985Monthly Fee: $2,172 Tax: $4,735 (2025)Community: Harbour Villa Club At The BuccaneerSpa: YesCondo
Taxes:$4,735
Remarks: Paradise Found: Fully Renovated Luxury at Harbour Villa Club, a True Longboat Key Gem! Welcome to a slice of heaven on the pristine North-End of Longboat Key at Harbour Villa Club. This luxurious, fully renovated (2025, not from storms) waterfront condo offers a lifestyle of serene elegance, perfectly positioned to capture breathtaking, unobstructed views of the glistening Sarasota Bay, the Intracoastal Waterway, and the protected Sister Keys. Step inside this exquisite home to an open, spacious floor plan bathed in natural light, thanks to high ceilings and expansive sliders. The custom gourmet kitchen is a chef's dream, featuring top-of-the-line appliances, ample counter space, and intelligent, creative storage solutions. The main living area is complemented by a sleek and stylish wet bar, ideal for effortless entertaining. The primary suite is a private sanctuary, designed for ultimate comfort with tremendous space, dual closets, and unparalleled water views. The equally luxurious primary bathroom features high-end fixtures, beautiful tile work, and a spacious shower. The secondary bedroom provides a generous space perfect for use as a guest suite or a flexible office. Relax or entertain year-round on your covered and screened lanai, the perfect outdoor space for sipping your morning coffee or evening cocktail while taking in the surrounding beauty. Boater's Dream and Unrivaled Flexibility: A rare and highly valuable amenity is the deeded boat slip #14, which conveys with the condo. This 40ft slip, equipped with electric, water, and new composite decking, is positioned directly outside the unit and can accommodate up to a 55'+/- vessel. Furthermore, Harbour Villa Club is one of the few Longboat Key communities with Weekly rental allowance, offering exceptional flexibility for ownership and use. Potentially generating gross approx. income of $85K annually with generous owner use availability. Community & Location: The community boasts mature tropical landscaping and grounds. Amenities include a heated pool, hot tub, outdoor grill, kayak storage/launch, boat ramp, climate-controlled bicycle/locker storage, and brand new tennis and pickleball courts. Located just a short walk to popular beaches, restaurants, and parks, and a short drive to St. Armands Circle and Downtown Sarasota. This property is more than a luxury condo—it is a complete lifestyle.
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Jesse Griffin (941-822-6165)
635 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228
$2,895,000151 Days on yellowkey MLS ID: A4679064
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3047 Built: 2025 Tax: $4,831 (2024)Community: Mary Regina ReeseSpa: NoSingle Family
Taxes:$4,831
Remarks: This gorgeous modern, elevated new 2025 masterpiece on fabulous Longboat Key has just made a significant price reduction! Built to the utmost of standards by the owners vision for his own family, (he is a also builder), this home has it all. Let’s start with the heavy custom front door surrounded by gorgeous large scale tiles in colors of the sea, that opens to the expansive great room, dining area and huge chefs kitchen. The kitchen is an entertainers dream, with a 5 burner gas range, pot filler, double ovens, built-in microwave and full size side by side refrigerator/freezer. A large center island provides ample storage and incredible work space, and of course there is a walk-in pantry and a separate area for a coffee and a wine fridge. Off of the kitchen and living/dining area is a screened in porch with a full outdoor kitchen for outdoor dining as well as an open porch with steps to the lush green grass. The primary suite is on this level, and a half bath and a gorgeous ensuite. The ensuite features an abundance of light with double sinks, a large double shower and a soaking tub. When you head up the staircase to the 2nd level, you will certainly notice the continuance of the incredible finishes and modern original light fixtures! Here you find a large landing with sliders to the enticing outdoor deck, perfect for your morning workout overlooking the beautiful neighborhood or just a spot for some sunset sky watching or midnight stars. 3 bedrooms, two with a jack and jill and one with a full ensuite make easy use of the space for all of your family and friends. Room for a pool on the side yard, plus deeded beach access across Gulf of Mexico Drive, make this a contemporary beach house to remember! This special, walkable mid-key location puts multiple dining, shopping and wildlife exploring destinations right at your doorstep, but you also have the opportunity for the world-renowned St.Regis Resort, St. Armands Circle and the cultural epicenter of Downtown Sarasota within a short drive. This is truly a lifestyle worth exploring. Make your private appointment today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
6001 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$9,995,000261 Days on yellowkey MLS ID: A4667111
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 6959 Built: 2013 Tax: $105,194 (2024)Community: Longboat KeySpa: YesSingle Family
Taxes:$105,194
Remarks: A Gulf-Front Masterpiece on Longboat Key! This stunning Gulf-front estate is perfectly placed on nearly an acre of pristine Gulf-front property along the shoreline on Longboat Key. With direct Gulf frontage, this architectural masterpiece offers more than 6,900 square feet of refined interiors and panoramic views that stretch endlessly across the Gulf of Mexico. Designed for both privacy and grand-scale entertaining, the residence balances timeless craftsmanship with recent enhancements including a 2025 primary bath remodel, newer French doors, and resort-style pool and spa with natural gas heating and fire pit. From the moment you arrive through the circular drive, the home’s elegant façade, manicured landscaping, and elevated design make a commanding first impression. Inside, expansive living areas are defined by travertine and hardwood flooring, soaring coffered ceilings, crown molding, and walls of glass framing breathtaking views. The open floor plan flows effortlessly from the formal living and dining rooms to the family room and gourmet kitchen, designed for effortless entertaining. The chef’s kitchen showcases custom wood cabinetry, granite counters, a large island, high-end appliances, double ovens, and a breakfast nook overlooking the Gulf. The main-floor primary suite offers a serene retreat with direct beach views, its own private terrace, dual walk-in closets, and a spa-like new bath featuring dual vanities, stone counters, and a freestanding soaking tub. A private elevator connects all levels, including a versatile second-story loft, media room, and four additional bedrooms (some en-suite) providing ample comfort for family and guests. The outdoor living space defines Florida luxury—complete with an expansive travertine deck, heated pool and spa, summer kitchen, and multiple covered terraces designed for dining and relaxation. Enjoy vibrant sunsets over the Gulf from nearly every vantage point. The property also features new hurricane-rated French doors, a whole-house generator with raised platform, and a three-car side-entry garage with guest parking. Located on the prestigious north end of Longboat Key, this gated estate offers the perfect balance of seclusion and accessibility. Stroll along miles of private beach or take a short drive to the Longboat Key Club, offering championship golf, tennis, and fine dining. Just minutes away, St. Armands Circle and downtown Sarasota offer a vibrant mix of boutique shopping, art galleries, and acclaimed restaurants. With world-class marinas, cultural landmarks, and pristine beaches within reach, this exceptional residence captures the very best of Sarasota’s luxury coastal lifestyle. Offering an unparalleled combination of design, craftsmanship, and Gulf-front serenity, 6001 Gulf of Mexico Drive stands as a statement of timeless coastal elegance—where every sunset feels like home.
Listing Agent: Roger Pettingell (941-387-1840)
554 SPANISH DR S, LONGBOAT KEY, FL 34228
$435,00085 Days on yellowkey MLS ID: A4688632
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1326 Built: 1971 Tax: $2,179 (2025)Community: Spanish Main Yacht Club CondoCondo
Taxes:$2,179
Remarks: Virtually Staged. Welcome to Spanish Main Yacht Club waterfront community and your new home! Light and bright, this stand-alone villa is all new and beautifully updated in 2026. White marble-like large porcelain tile floors that span the entire living area, providing a continuous flow throughout the villa. The new kitchen boasts stainless steel appliances, white quartz countertops, new cabinetry, lighting and more. Attractive updates in the primary en suite bedroom and guest bath as well. A nice added feature is the spacious interior laundry room. Beautiful, lush backyard view with privacy and an extra brick paver side yard and outdoor space. A short stroll to the privately deeded beach entrance to gorgeous Gulf beaches. Two minutes to have your toes in the soft, pearly sand. This is a boater’s paradise with slips available for an extremely inexpensive lease and direct access to Sarasota Bay, the Intracoastal waterway and azure waters of the Gulf. Only a short drive to the fantastic shops, restaurants and cultural events Sarasota and St. Armands Circle have to offer. This is a great investment opportunity and chance to enjoy Longboat Key living. The community is in the build-back stage due to damage from hurricanes in 2024 and is almost complete. All 212 units in Spanish Main are under FEMA requirements, guidelines, and stringent adherence to rebuild specifications and inspections from Town of Longboat Key. This is an opportunity to continue to make this villa your custom home.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Kimberly Freiwald (941-256-6775)
6680 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$13,499,000134 Days on yellowkey MLS ID: A4682193
Bed: 6 Bath: 6.5 Gar: 6 Liv Area Sq Ft: 6408 Built: 2020 Tax: $22,777 (2025)Community: RauchSpa: YesSingle Family
Taxes:$22,777
Remarks: Welcome to a once-in-a-generation private waterfront family compound on the coveted north end of Longboat Key—an extraordinary 2.4 acre, fully gated coastal estate that blends architectural mastery, resort-level amenities, and rare development potential. Encompassing four buildable parcels (500, 510, 520 Nomas Way and 6680 Gulf of Mexico Drive), this legacy property offers unparalleled privacy, flexibility, and long-term value. From the moment you arrive, illuminated by classic Bevelo gas lanterns, the estate unfolds with intention and elegance. The custom-designed main residence is complemented by a separate 3-bedroom, 2-bath, 1,850-sq-ft guest home with a detached garage—perfect for extended family, guests, or staff accommodations. Every detail reflects thoughtful craftsmanship, from the 900-bottle red cedar wine cellar to the oversized custom wood-burning fireplace with gas option. Designed for both grand entertaining and everyday indulgence, the chef’s kitchen features natural gas cooking with Wolf and Sub-Zero appliances, while state-of-the-art home automation and whole-home sound elevate daily living. Step outside to a true private resort: a 15,000-gallon free-form pool with a 1,000-gallon spa, heating and chilling via reverse heat pump and natural gas, and an expansive custom tiki pavilion built for unforgettable gatherings. For boating enthusiasts, this estate is unmatched—165 feet of frontage on Bishops Bayou, two docks, three boat lifts, and deep-water, direct Intracoastal access. Across Gulf of Mexico Drive, deeded private beach access makes turquoise waters and nightly sunsets a daily ritual. Car collectors and hobbyists will appreciate six garages, including an automotive lift, plus a 50’ x 24’ covered pole barn for additional storage. Peace of mind is absolute with a 24-camera security system, safe room, elevator, and a 60kW natural gas generator powering the entire estate during any weather event. Fully fenced and gated, this property offers complete privacy without compromise. This is more than a home—it is a coastal masterpiece, a designer’s dream that exudes sophistication, balance, and harmony. An irreplaceable opportunity to own one of Longboat Key’s most remarkable waterfront estates, where luxury, security, and lifestyle converge in perfect alignment.
Listing Agent: Lee Brewer (941-724-3448)
791 BROADWAY ST, LONGBOAT KEY, FL 34228
$1,625,00037 Days on yellowkey MLS ID: A4694059
Bed: 2 Bath: 2.0 Gar: 4 Liv Area Sq Ft: 2236 Built: 1995 Tax: $9,600 (2025)Community: Longbeach VillageSingle Family
Taxes:$9,600
Remarks: Welcome home to 791 Broadway, nestled in the heart of historic Longbeach Village on the North end of prestigious Longboat Key. This elevated island-style residence offers the perfect blend of coastal charm, comfort, and relaxed island living. Thoughtfully designed across multiple levels including a large 11x30 third floor FLEX SPACE that could easily be converted into a 3RD BEDROOM. This home captures beautiful morning sunrises, colorful sunsets, and stunning views of Sarasota Bay and the intracoastal waterway. From the moment you step inside, you are greeted by an abundance of natural light, soaring ceilings, plantation shutters, and inviting open spaces that are ideal for both everyday living and entertaining. The property offers wonderful flexibility, including an oversized garage with plenty of room for golf carts, kayaks, bicycles, beach gear, and more. The outdoor living areas are equally inviting, with several unique spaces to relax and enjoy the surroundings — from the covered front porch to the rear deck overlooking the water, along with the peaceful sound of multiple water features throughout the property. Recent updates add comfort and peace of mind, including new impact-resistant and energy-efficient windows, two AC units, updated flooring, and many additional improvements that make this home feel warm, welcoming, and move-in ready. Enjoy the charm and convenience of the Village, just a short stroll from community fishing piers, a boat launch, exceptional dining, and the white sandy beaches and turquoise waters of the Gulf of Mexico. This is a wonderful opportunity to experience the laid-back Longboat Key lifestyle in one of the island’s most beloved neighborhoods.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Matthew Voss (941-402-8799)
5231 GULF OF MEXICO DR #104, LONGBOAT KEY, FL 34228
$499,000175 Days on yellowkey MLS ID: A4676730
REDUCED by $46,000 (8.4%) on 06/15/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 720 Built: 1973 Tax: $6,784 (2024)Community: Covert IiCondo
Taxes:$6,784
Remarks: Have you dreamed of the perfect island getaway situated right on a gorgeous stretch of beach on Longboat Key? This is by far the lowest priced direct beachfront condo on the entire island and it is already completely updated! Whether you decide to use it yourself or use it as an investment with outstanding monthly rental income availability, this is the one. With a fabulous ground floor location, you can have your toes in the sand in only a few steps! This condo offers Italian porcelain tile throughout and a completely new kitchen with beautiful counter tops, all new cabinets and new appliances. The bathroom has been beautifully updated as well and features custom tile work in a seaside theme. The view is fabulous in either direction with the sparkling pool out front and the gorgeous Gulf of Mexico out back. The open living and dining area allows plenty of space to entertain or to quietly contemplate whether it’s a beach day, a day for a soak in the pool or a walk to the Covert bayside fishing pier. The bedroom offers the same stunning beach view and features storm rated sliders to the screened in lanai. The midkey location allows for easy access to multiple restaurants and shopping. The tree filled mangrove trails of Joan Durante Park are a birders’ paradise and the 12 mile long bike path give you many options to soak in the sun while getting in your daily exercise. This is island living at its best at a price you may never thought you could find!
490 N SHORE RD #6, LONGBOAT KEY, FL 34228
$699,000344 Days on yellowkey MLS ID: A4657668
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1350 Built: 1978 Tax: $4,481 (2024)Community: Northgate Of Longboat KeySpa: NoCondo
Taxes:$4,481
Remarks: This rare offering is all about the one-of-a-kind BREATHTAKING VIEWS overlooking multiple waterways across Greer island, towards the Intracoastal and out to the gorgeous Gulf of Mexico sunsets! Situated on the quiet north end of Longboat Key in a boutique waterfront, building containing only 9 townhouse style residences: this is island living at its best! It features two bedrooms and 2 and a half baths plus a bonus ground floor air conditioned room and a workshop. Take the steps up to your first living level and enjoy a galley kitchen open to the large great room with sliders to one of 2 outdoor balconies above the ground level, poolside covered porch. On this level is also a half bath. Take the steps up to the second level and the views become even more astounding through the sliders from the Primary ensuite bedroom! Here you will also find the 2nd bedroom and the second bath. Besides the sparkling waterside pool, this small and friendly community has 3 small docks available that allow for easy water access with your kayak, paddleboard or small boat. And don’t forget it has its own clay tennis court as well. One of the nicest and widest beaches on Longboat Key is located just down the street and it wraps all the way around Greer island where you can stand and admire your condo across the waterway from your walk! Multiple restaurants and shopping destinations are within a bike ride or short walk away and the cultural epicenter of downtown Sarasota and Bradenton are just off island when you choose to leave. This may well be the laid-back island life style you are searching for.
729 SAINT JUDES DR S #3, LONGBOAT KEY, FL 34228
$449,000106 Days on yellowkey MLS ID: A4685189
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 630 Built: 1966 Tax: $1,994 (2025)Community: Saint Judes AptsSpa: NoCondo
Taxes:$1,994
Remarks: Live that Longboat Key waterfront lifestyle and have your own boat lift without the multi-million dollar price. Cute and conveniently located, this on-grade one bedroom condominium unit that is located on a saltwater canal on Longboat Key, features its own 10,000 lb boat lift, and is one block to the gulf beaches and adjacent to Durante Park. Everything new in 2025, including a washer and dryer and hot water demand unit. The condo is completely furnished with an updated living space, complete with open kitchen that features granite countertops, stainless steel appliance and plenty of storage. The modern wood-look tile and updated sliders and windows make for an open feeling living area. There is a paver patio and dock behind the condo for enjoying the sunsets on the canal. A number of shops and restaurants within walking distance. Schedule your showing today!
Listing Agent: Steven Schield (941-650-1010)
311 FIREHOUSE CT, LONGBOAT KEY, FL 34228
$2,399,000276 Days on yellowkey MLS ID: A4665445
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2352 Built: 2005Monthly Fee: $467 Tax: $29,195 (2025)Community: Conrad BeachSingle Family
Taxes:$29,195
Remarks: NEWLY PRESENTED & FULLY FURNISHED. Some homes invite you to exhale the moment you arrive. This is one of them. Nestled within the award-winning Conrad Beach community on Longboat Key — ideally positioned west of Gulf of Mexico Drive — this elevated coastal residence is offered fully furnished as a true Gulf Coast retreat. Set within an intimate enclave of architect-designed homes, it delivers a rare combination of privacy, tranquility, and timeless coastal character that grows harder to find with each passing season. Designed for effortless island living, the home pairs classic coastal architecture with resort-inspired interiors and a relaxed elegance that feels both welcoming and refined. Mornings begin with coffee on the porch as tropical landscaping sways in the Gulf breeze. Evenings unfold on the upper west-facing deck as golden light dissolves into the water. Thoughtfully designed landscape lighting transforms the grounds after dark, making every night feel like an occasion. Inside, freshly refreshed interiors are curated for comfort, connection, and easy entertaining. The gourmet kitchen anchors the home around an oversized quartz island where guests naturally gather. Open-concept living spaces flow seamlessly outdoors, while a spacious lanai extends the entertaining footprint — with flexibility for future enclosure if desired. The main-level primary suite offers a peaceful escape with its own private balcony overlooking lush tropical surroundings. Upstairs, guest bedrooms and a loft-style family room accommodate visitors with ease — equally suited to seasonal stays, remote work, or multi-generational living. A two-car garage supports a true lock-and-leave lifestyle, while Firehouse Court's no street parking policy preserves the quiet, residential character of the neighborhood. Community amenities include a resort-style pool, entertaining areas, bath facilities, and observation spaces — all maintained through remarkably low HOA fees that cover lawn care, landscaping, irrigation, and common area upkeep. For peace of mind, the home is equipped with high-impact windows and doors, a whole-house fire sprinkler system, and a full-house generator. For buyers seeking relief from crowded beaches and hurried routines, the contrast is immediate — life here is open, unhurried, and ready to enjoy from day one. Just over the bridge, Anna Maria Island offers waterfront dining, boutique shopping, and the kind of authentic Old Florida charm that keeps everyone coming back. Minutes from the pristine beaches of Longboat Key's coveted north end, this is more than a home. It's where lasting memories are made, priorities reset, and a life you've been waiting to live finally begins.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Kathy Harman (941-900-9828)
701 SAINT JUDES DR S #3, LONGBOAT KEY, FL 34228
$259,000177 Days on yellowkey MLS ID: O6370226
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 630 Built: 1966Monthly Fee: $787 Tax: $3,873 (2024)Community: Saint Judes AptsSpa: NoCondo
Taxes:$3,873
Remarks: DIRECT WATERFRONT OPPORTUNITY IN LONGBOAT KEY! Here's your rare chance to own a waterfront property with direct access to the Intercoastal Waterway! Perfectly located for vacation rentals, this canal-front 1-bedroom, 1-bathroom end unit offers incredible potential for income, especially with high demand bookings from January to April. This property boasts 21 feet of water frontage and a newly installed seawall (June 2021). Enjoy the Florida lifestyle with easy access to boating, kayaking, and fishing. Additional outdoor amenities include a paver patio. Just steps away from the beach access and kayak launch! The property also has direct access to the scenic Joan M. Durante Park, with 32 acres of walking trails, gardens, recreational areas, and breathtaking Sarasota Bay views. Take a short walk to top-rated restaurants, shops, a deli, bike and kayak rentals, and more. Plus, you're just a short drive to St. Armands Circle and Anna Maria Island! This is the most economical waterfront property you'll find in all of Longboat Key!
Listing is courtesy of: NIZZ REALTY INC (954-526-5105)
Listing Agent: Filitsa Sterner Mistretta (941-928-3666)
900 SPANISH DR N, LONGBOAT KEY, FL 34228
$750,00065 Days on yellowkey MLS ID: A4690879
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1423 Built: 1971 Tax: $4,203 (2025)Community: Spanish Main Yacht Club CondoSpa: NoVilla
Taxes:$4,203
Remarks: This must-see hidden gem on the north end of Longboat Key offers a quintessential Florida lifestyle. Waterview’s galore as you walk into your newly completed, renovated Florida paradise home, on a deepwater marina and canal, which epitomizes beauty and style. Boat lovers will want the location of this totally turnkey furnished 1,423-square-foot standalone two-bedroom, two-bath home, with your upgraded composite boat dock just 15 feet behind your villa. Completely remodeled, this home provides contemporary classic design features that create an open airy gorgeous living space. All new stainless appliances in 2026, air-conditioner 2025, roof 2019 and more. The open kitchen design with a large island, new quartz countertops, plenty of beautiful new cabinets with roll-out drawers and a contrasting white and gray classic color scheme. Great counter space makes the kitchen ideal for entertaining and enjoying the coastal casual lifestyle. Beautiful porcelain tile flows throughout the home, providing continuity from room to room. An oversized skylight in the great room with retractable shade provides lots of extra natural brightness. The large primary bedroom is complete with a fully refashioned en-suite bath with gorgeous granite countertops and custom-tiled shower. A spacious walk-in closet provides plenty of room for your coastal style wardrobe. The second bath mimics the maintained class and elegance of this home with granite counters and tiled shower. The lanai has been transformed into extra living space with a cozy study and separate office nook. The study is an ideal spot to curl up with a book or just sit privately and watch the beautiful white pelicans float by with dolphins and manatees alongside. This flexplace can also house extra sleepover guests. The double lanai facing the water allows a panoramic view and full access to your large, elevated brick paver patio and dock from floor-to-ceiling, impact-grade patio doors. Go outside to a private oasis that overlooks the wide-open canal, marina and bay views. Sit, dine, entertain or sunbathe while you enjoy the abundant wildlife from the comfort of your patio paradise, or hop in your boat secured to your 5-by-25-foot dock and head out to one of the many Longboat Key restaurants. Some of the best waters to explore in Sarasota for fishing, sandbar enjoyment, kayaking and swimming right in your backyard. You have direct access to the Intracoastal Waterway and a quick boat ride to the Gulf of Mexico. Impact windows and new hurricane-rated doors throughout. The Spanish Main maintenance-free community has a wonderful neighborhood feel with heated pool, deeded beach access, a 40-foot slip marina with social events galore, making every day feel like a vacation as you lounge in the sun poolside and enjoy the sea The deeded beach access is ideal for those numerous beach days and magnificent sunsets. Pet-friendly, maintenance-free, and an active 55-plus community are added benefits for your enjoyment. Only a short drive to fantastic shops and restaurants, including Anna Maria Island, plus cultural events Sarasota and St. Armands Circle have to offer. This villa has been fully renovated in compliance with FEMA standards due to hurricane flooding in 2024.
333 FIREHOUSE CT, LONGBOAT KEY, FL 34228
$2,325,000220 Days on yellowkey MLS ID: A4672573
REDUCED by $170,000 (6.8%) on 06/01/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2900 Built: 2016Monthly Fee: $467 Tax: $10,420 (2024)Community: Conrad BeachSpa: NoSingle Family
Taxes:$10,420
Remarks: Virtually Staged. Experience the best of Longboat Key living in this elevated coastal retreat, ideally located in the desirable Conrad Beach community just a block from the Gulf of Mexico. Designed with timeless style and modern comfort in mind, this 4-bedroom, 4.5-bath residence offers sophisticated finishes, smart upgrades, and all the pleasures of island life without the upkeep of a private pool. Spanning 2,900 square feet, the open-concept layout showcases a chef’s kitchen with an oversized quartz island, premium appliances, and generous counter space ideal for entertaining family and friends. Light-filled second-level living and dining spaces open to an expansive porch and outdoor dining space , creating a seamless indoor-outdoor flow. The first living level features a serene primary suite with a spa-inspired bath and private balcony, offering a peaceful retreat. Upstairs guest suites provide privacy and comfort, with terraces to capture the island’s cooling breezes and glowing Gulf sunsets. A stunning rooftop deck with jacuzzi crowns the home, creating an unforgettable setting for evening relaxation or gatherings under the stars. Additional highlights include impact-rated windows and doors, elevator ready, and a two-car garage with ample storage. The award-winning Conrad Beach community offers a recently renovated resort-style pool with bath facilities and beautifully maintained landscaping, all just a short stroll from the shoreline. Enjoy the vibrant charm of nearby Anna Maria Island, Longbeach Village dining, marinas, and boutique shopping at St. Armands Circle and Sarasota. This home blends coastal sophistication, privacy, and comfort—an ideal winter haven to share with family and friends.
Listing Agent: Steve Walter (941-809-0907)
515 FOREST WAY, LONGBOAT KEY, FL 34228
$1,420,000154 Days on yellowkey MLS ID: A4679679
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2880 Built: 1989Monthly Fee: $1,698 Tax: $4,802 (2025)Community: Cedars East Sec 2Spa: NoCondo
Taxes:$4,802
Remarks: NEW PRICE, AMAZING OPPORTUNITY!!! Experience the ultimate island lifestyle in this masterfully renovated 2,880 sqft, 4 Bed/3 Bath "lock-and-leave" condo at Cedars Tennis Resort and Club. Elevated sanctuary on the tranquil north end of Longboat Key. Offering the expansive feel of a single-family residence with the effortless "lock-and-leave" ease of being in the beautiful condo community of Cedars Tennis Resort and Club. This exquisite 4BR/3BA retreat defines coastal chic. A private elevator serves all three levels, opening into a sun-drenched great room with soaring ceilings, a fireplace, and a gourmet kitchen featuring dual islands and designer finishes. The refined dining room opens right off of this space with its custom built-in cabinetry and dry bar, ideal for any social gathering. Relax on your private, screened lanais overlooking lush tropical foliage and serene ponds, with peek-a-boo views of the Gulf. There is one on each living level. Rounding out the main living area is a versatile den/office (currently used as the 4th bedroom), a full third bathroom, beautiful hardwood floors throughout and a dedicated laundry room. The primary suite is a true oasis with a spa-inspired sunken bath, large walk-in shower, dual vanities and walk-in closets. Upstairs beyond the oasis of a primary there are two additional oversized guest bedrooms and a beautifully renovated guest bathroom with a walk-in shower. Recent updates beyond the full interior renovation include 2026 garage door replacements, and 2024 roof and AC replacement. Hardi- Board siding on exterior and Pella high-impact windows. The split 3-car garage provides total peace of mind and the rare abundance of space and storage. Nestled in the 66-acre village-like townhome community enveloped by nature, providing effortless access to both the beach and the bay on the beautiful north end of Longboat Key. The spacious and tropical community features lit boardwalks winding through mangroves, leading to an array of exceptional amenities including a heated Jr. Olympic Size Pool, nine Har-Tru Tennis Courts, three Pickleball courts, a Clubhouse with a Pro-Shop, a 24-hour Fitness Center, a Tiki bar, a restaurant, a fishing pier, and a kayak launch. Please note that some amenities require an additional club membership. The property is within walking distance to a variety of local attractions, such as Harry's Deli & Continental Kitchen, the true island gem that is Joan Durante Park, Euphemia Haye Restaurant & The Haye Loft, and, of course, Longboat Key's globally renowned sugary white sand beaches. Furthermore, it offers convenient proximity to other major attractions and cultural venues, including St. Armand's Circle, Mote Aquarium, the Asolo Repertory Theatre, Van Zel Performing Arts Center, Marie Selby Gardens, Anna Maria Island, the Ringling Museum complex, and numerous dining options on Longboat Key and in downtown Sarasota. Cedars East is the rare community on LBK that offers shorter-term rental allowance with its 2-week minimum, making it the perfect balance for offsetting costs when not in use, without living in a hotel community. Exceptional onsite management is in place if desired. Fantastic residence, rare opportunity, come take a look today!
602 SPANISH DR S #115, LONGBOAT KEY, FL 34228
$379,90036 Days on yellowkey MLS ID: A4694415
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1427 Built: 1969 Tax: $2,667 (2025)Community: Spanish Main Yacht Club CondoCondo
Taxes:$2,667
Remarks: Welcome to Spanish Main Yacht Club, one of Longboat Key's most beloved waterfront communities, where 55-plus living unfolds at an easy, unhurried pace between the Gulf of Mexico and Sarasota Bay. Tucked along a quiet street lined with tidy single-story villas and swaying palms, this fully renovated two-bedroom retreat captures the old-Florida charm that makes this island enclave so special, paired with the fresh, move-in-ready updates. Behind the arched front entry and crisp white stucco exterior with its white tile roof, a bright open interior welcomes you, where neutral tile floors run throughout and natural light pours through plantation-shuttered windows. The renovated kitchen is the heart of the home, outfitted with white shaker cabinetry, quartz countertops, a waterfall-edged peninsula, a soft glass-tile backsplash, and crisp white appliances, all opening to a generous living and dining area finished with crown molding and an easy coastal feel. A versatile bonus room wrapped in windows, with a door to the back patio, makes a wonderful sunroom, reading retreat, or home office. Both bedrooms are comfortable and well-appointed, served by two beautifully updated bathrooms, one with a tub and shower framed in subway tile, the other a glass walk-in shower with a mosaic floor and designer fixtures. A covered carport with room for a golf cart, plus interior storage for kayaks and beach gear, adds everyday ease. Brick paver walkways and lush tropical landscaping wrap the home, and the concrete tile roof is just over five years young. Life at Spanish Main is built around the water and the warmth of neighbors. Residents enjoy a heated pool overlooking the basin, a clubhouse, shuffleboard courts, kayak storage and launch, and a deep-water marina with boat slips available for a monthly fee, offering quick access to Sarasota Bay and the Gulf beyond. Best of all is the community's private Gulf beach access, just a short stroll away, along with shaded benches lining the lagoon and a waterfront green where slow mornings and golden evenings by the water become a way of life. Beyond the community, the white sand of Longboat Key's Gulf beaches is moments away, with the boutiques and dining of St. Armands Circle, downtown Sarasota's culture, and the laid-back charm of Anna Maria Island all within easy reach. Come experience the rare blend of comfort, community, and coastal beauty that makes this villa a place to call home. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Toni Zarghami (941-248-2147)
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